在多功能催化作用下，α，β-不饱和酮与γ-丁内酯的不对称乙烯基迈克尔加成反应。

Asymmetric vinylogous Michael reaction of alpha,beta-unsaturated ketones with gamma-butenolide under multifunctional catalysis.

机构信息

Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

出版信息

Chem Commun (Camb). 2010 Aug 28;46(32):5957-9. doi: 10.1039/c0cc01054e. Epub 2010 Jul 2.

DOI:10.1039/c0cc01054e

PMID:20601978

Abstract

A general and direct organocatalytic asymmetric vinylogous Michael reaction of gamma-butenolide with alpha,beta-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile gamma-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30:1 dr and 95-99% ee).

摘要

研究了一种多功能伯胺盐作为催化剂的γ-丁内酯与α,β-不饱和酮的一般性和直接的有机催化不对称乙烯基迈克尔加成反应。该反应可以从简单的 2(5H)-呋喃酮直接获得合成多功能γ-取代丁内酯，产率、非对映选择性和对映选择性都令人满意（最高达 30:1 dr 和 95-99%ee）。